The class of cyclic enones is well known in organic chemistry. Best known examples of cyclic enones are quinones such as, for example, the benzoquinones, naphthoquinones, anthraquinones, phenanthraquinones, and the like. 1,4-Benzoquinone is commonly referred to as quinone. Quinones are generally brightly colored compounds and have versatile applications in chemical synthesis, biological uses, as redox materials, as well as in industry. There are several review articles on the chemistry and applications of quinones including, for example, Kirk-Othmer Encyclopedia of Chemical Technology, Third ed., Vol. 19, pages 572-605, John Wiley & Sons, New York, 1982.
The synthesis of quinones is well documented. See, for example, J. Cason, Synthesis of Benzoquinones by Oxidation, in Organic Synthesis, Vol. IV, page 305, John Wiley & Sons, New York (1948). Quinones generally are prepared by oxidizing the appropriately disubstituted aromatic hydrocarbon derivatives, the substituents being hydroxyl or amino groups in the ortho or para positions. 1,4-Benzoquinone, for example, can be made from the oxidation of hydroquinone, p-aminophenol or p-phenylenediamine, or from quinic acid. The reagents generally used for the oxidation are dichromate/sulfuric acid mixture, ferric chloride, silver (II) oxide or ceric ammonium nitrate. In these cases, oxidation of the aminoaromatic compound is accompanied by hydrolysis to the corresponding quinone. Some processes may take several hours for completion of the reaction.
Thus, some of the prior art processes utilize a catalytic agent to achieve an acceptable reaction rate while other processes proceed without catalysts. The process according to the present invention utilizes a hypochlorite reagent which provides extremely high conversion, high selectivity, and fast reaction rates to prepare a quinoneimine.
A prior art process which utilizes a catalyst in the preparation of a quinoneimine compound is disclosed by Desmurs, et al. in U.S. Pat. No. 5,189,218. The process of Desmurs, et al., which converts N-(4-hydroxyphenyl)aniline into N-phenylbenzoquinone-imine, utilizes a manganese, copper, cobalt, and/or nickel compound as a catalyst in an oxidation type reaction.
The above process of Desmurs, et al., which uses a metal catalytic component, along with any other processes which utilize a metal catalyst, have several drawbacks. Not only are the metal catalysts relatively expensive, they raise important environmental concerns. For example, effluent streams and products can be contaminated by the metals. Further, recovery of the catalyst for reuse can be prohibitively expensive.
Other processes are known which use oxidizing agents to convert phenylenediamines into their corresponding quinonediimines. For example, EP 708,081 (Bernhardt et al), which describes the conversion of phenylenediamines to phenylenediimines by oxidation of the diamine in an alkali/alcoholic solution, gives a general description of such processes in its background. The EP '081 process suffers from various disadvantages including long reaction times and low yields.
An oxidation process for the catalytic oxidation of hydroxy containing aromatic compounds to form their respective quinone compounds is described by Parker in U.S. Pat. No. 5,091,545. Parker teaches the use of catalytic cobalt, a primary aliphatic amine and an alcohol to convert a hydroxy containing aromatic compound to the corresponding quinone compounds.
Additional oxidation conversion processes are described by Wheeler in U.S. Pat. No. 5,118,807, by GB 1,267,635, and by Haas et al, in EP 708,080. However, the use of a hypochlorite as an oxidizing agent in the conversion of hydroxyphenylamine compounds to give highly selective yields of N-substituted-quinoneimine compounds has not heretofore been suggested.
As such, the current invention is based on the problem of providing a simple and economic process for the preparation of N-substituted-quinoneimines in high yields and with high selectivity.